Enantioselective Aza-Reformatsky Reaction with Ketimines

Here, an enantioselective aza-Reformatsky reaction using acyclic ketimine substrates is presented. Using α-phosphorated ketimines as electrophilic substrates and a simple BINOL-derived ligand, phosphorated analogues of aspartic acid holding chiral tetrasubstituted carbons are efficiently obtained wi...

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Detalles Bibliográficos
Autores: Maestro Burzaco, Aitor, Palacios Gambra, Francisco Javier, Martínez de Marigorta Izaga, Edorta, Vicario Hernando, Javier
Tipo de recurso: artículo
Fecha de publicación:2019
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/70066
Acceso en línea:http://hdl.handle.net/10810/70066
Access Level:acceso abierto
Palabra clave:asymmetric catalysis
alpha-aminophosphonates
beta-lactams
imines
Reformatsky reaction
organophosphorus compounds
Descripción
Sumario:Here, an enantioselective aza-Reformatsky reaction using acyclic ketimine substrates is presented. Using α-phosphorated ketimines as electrophilic substrates and a simple BINOL-derived ligand, phosphorated analogues of aspartic acid holding chiral tetrasubstituted carbons are efficiently obtained with excellent enantioselectivity through an asymmetric organocatalytic Reformatsky-type reaction. The phosphorated analogues of aspartic acid have been used for the synthesis of phosphorus-containing enantiopure tetrasubstituted β-lactams.